Hexane → HCID 21993302, compound

Participants

Reaction Conditions

Reaction Steps

The above 5-propyl-2-(4-(3,5-difluorophenyl)cyclohexyl-1,3-dioxane 1.3 g (4.0 mmol) was dissolved in THF 10 ml, and cooled to −65° C. under a nitrogen atmosphere. To this solution, 1.68 M hexane solution 3.0 ml (5.0 mmol) of n-butyllithium was added dropwise keeping the liquid temperature below −55° C., and the mixture was stirred for one hour at the same temperature. Then, to the reactant, 0.5 M THF solution 10 ml (5.0 mmol) of zinc chloride was added dropwise keeping the liquid temperature below −50° C., and the mixture was heated to room temperature and stirred for 30 minutes. Tetrakistriphenylphosphin paradium 0.5 g and 3-fluoro-4-chlorobromobenzene 1.1 g (5.3 mmol) were added to the solution, and the mixture was refluxed with heating for 3 hours. Water 30 ml was added to the resulting reactant, and the product was extracted with toluene. The extract was washed with 3N-hydrochloric acid, a saturated bicarbonate aqueous solution and then a saturated sodium chloride aqueous solution, and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: toluene), and recrystallized twice from a mixed solvent of heptane/ethyl acetate=1/1 to obtain 5-propyl-2-(4-(4-(3-fluoro-4-chlorophenyl)-3,5-difluorophenyl) cyclohexyl)-1,3-dioxane 1.7 g (3.8 mmol). The yield was 95.0% from 5-propyl-2-(4-(3,5-difluorophenyl)ethyl)-1,3-dioxane.

Provenance & Evidence